Compositions and methods for reducing atmospheric ozone levels

ABSTRACT

Provided are ozone decomposing compositions comprising a solvent and a polymer. The polymer comprises a structural repeat unit comprising an unsubstituted or substituted carbohydrate moiety. Also provided are methods of decomposing ozone using the compositions, and spray coatings, items of clothing, fabrics, carpets, paints, sealants, finishes, air-filters, face-masks, cosmetics, creams, lotions and coatings incorporating the polymer.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of prior application Ser. No.14/821,710, filed Aug. 8, 2015, now U.S. Pat. No. 9,669,401B2, whichclaims the benefit of U.S. Provisional Application Ser. No. 62/034,864filed on Aug. 8, 2014, entitled “COMPOSITIONS AND METHODS FOR REDUCINGATMOSPHERIC OZONE LEVELS,” the entire disclosure of which isincorporated herein by reference.

FIELD OF THE INVENTION

The present disclosure is in the field of compositions and methods forcontrolling air pollution; and more particularly, the invention relatesto compositions and methods for reducing ozone levels.

BACKGROUND OF THE INVENTION

Ozone is formed in the atmosphere by the action of sunlight, ultravioletlight or an electrical discharge such as lightning on oxygen in the air.It is also formed when an electrical apparatus produces sparks in theair.

Ozone in the air may be toxic to human beings and animals. According toOccupational Safety and Health Administration (OSHA), the permissiblemaximal average concentration of ozone in the air should be no more than0.1 ppm when breathing air. Many apparatuses for industrial use aremanufactured in accordance with these standards. Ozone has acharacteristic odor, which is noticeable even at concentrations as lowas 0.01 to 0.02 ppm. When the concentration of ozone increases to about0.05 ppm, it has an unpleasant odor; and when the concentration exceeds0.1 ppm, it is irritating to the mucous membranes of the eyes andrespiratory organs. Ozone is also a powerful oxidizing agent whichoxidizes and deteriorates organic materials. Therefore, it is desirablethat the concentration of ozone be kept as low as possible.

Ozone is used in industry for the sterilization, deodorization anddecolorization of water and for the treatment of raw sewage. Theseapplications often require the use of ozone in concentrations as high as500-2500 ppm. For example, to sterilize water, 1 to 3 g of ozone isbubbled into 1 cubic meter of water. Most of the ozone blown into wateris decomposed, however, some of the residual ozone can be dischargedfrom the water into the air. Since the concentration of the dischargedozone in the air may be as high as 1 ppm, it is necessary to decomposethe discharged ozone before it spreads into the air for the safety tohuman beings and for the protection of the environment.

Since ozone is toxic to human beings when its concentration in the airis high, various methods have been proposed to decrease itsconcentration. For example, filters made of activated carbon and filterscontaining various catalysts, such as metal oxides of manganese, copper,silver and cobalt, have been employed for decomposing ozone. If thedensity of the materials in these filters is high, the absorption ofozone and its decomposition efficiency is increased. However, the higherdensity of these materials slows the flow rate of the air through thefilter. By contrast, if the density of the materials in the filter isdecreased, the absorption of ozone and the ozone decompositionefficiency are decreased.

Various polymers and terpenoid compounds have also been used to controlozone levels. For example, a rubber olefin polymer containing doublebond groups has been used for decomposing ozone generated from anelectrophotographic copying machine. Terpenoid compounds capable ofdecomposing ozone, such as linalool, linalool ester, citral and thelike, in various solutions and gels have also been used. In addition,paints containing a variety of organic materials have been proposed.However, the decomposition efficiency is not high enough for use inpractice. Furthermore, the by-products formed after decomposition of theozone has not been fully characterized in these cases. Therefore, it isunclear whether exposure to these by-products affect a person's health,and whether there are any negative environmental impacts.

Therefore, there remains a need in the art for new compounds,compositions and methods for removing and/or controlling ozone levelswithout having a negative impact on humans, animals and the environment,wherein the by-products formed after decomposition of the ozone is safeand fully characterized.

SUMMARY OF THE INVENTION

Disclosed herein are ozone reactive polymers comprising a structuralrepeat unit represented by the following formula XLI:

wherein A is absent or a linking group selected from the groupconsisting of substituted or unsubstituted alkylene, substituted orunsubstituted heteroalkylene, substituted or unsubstitutedcycloalkylene, substituted or unsubstituted heterocycloalkylene,substituted or unsubstituted arylene, substituted or unsubstitutedheteroarylene, substituted or unsubstituted arylalkylene, andsubstituted or unsubstituted heteroarylalkylene; each of R₁, R₂ and R₃is, independently, selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and whereinsaid structural repeat unit comprises at least 10% by weight of saidpolymer.

The present invention also provides an ozone decomposing compositioncomprising a solvent and a polymer of the present invention.

Further disclosed herein are methods of decomposing ozone comprisingcontacting ozone with an ozone decomposing composition of the presentinvention.

DETAILED DESCRIPTION OF THE INVENTION

Unless otherwise defined, scientific and technical terms used inconnection with the disclosure shall have the meanings that are commonlyunderstood by those of ordinary skill in the art. Further, unlessotherwise required by context, singular terms shall include pluralitiesand plural terms shall include the singular. The nomenclatures utilizedin connection with, and the laboratory procedures and techniques of,analytical chemistry, synthetic organic chemistry, and medicinal andpharmaceutical chemistry described herein are those well-known andcommonly used in the art. Standard techniques are used for chemicalsyntheses, chemical analyses, formulations, and delivery.

Abbreviations used herein have their conventional meaning within thechemical and biological arts.

Where substituent groups are specified by their conventional chemicalformulae, written from left to right, they equally encompass thechemically identical substituents that would result from writing thestructure from right to left, e.g., —OCH₂— is equivalent to —CH₂O—.

The term “alkyl” by itself or as part of another substituent, means,unless otherwise stated, a straight unbranched or branched chain, or acyclic hydrocarbon radical, or a combination thereof, which may be fullysaturated, mono- or polyunsaturated and can include di- and multivalentradicals having the number of carbon atoms designated, e.g. C₁-C₁₀ meansone to ten carbons. Examples of saturated alkyl groups include, but arenot limited to, groups such as methyl, ethyl, n-propyl, isopropyl,n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl,n-octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,(cyclohexyl)methyl, cyclopropylmethyl and the like. An unsaturated alkylgroup is one having one or more double bonds or triple bonds, i.e.alkenyl and alkynyl groups. Examples of unsaturated alkyl groupsinclude, but are not limited to, vinyl, 2-propenyl, crotyl,2-isopentenyl, 2-(butadienyl), 2,4-pentadienyl, 3-(1,4-pentadienyl),ethynyl, 1- and 3-propynyl, 3-butynyl, and the like.

The term “alkylene” by itself or as part of another substituent means adivalent radical derived from an alkyl group, i.e. alkyl, alkenyl andalkynyl groups, as exemplified, but not limited, by —CH₂CH₂CH₂CH₂—,—CH₂CH═CHCH₂—, —CH₂C═C═CH₂—, —CH₂CH₂CH(CH₂CH₂CH₃)CH₂—. In oneembodiment, an alkyl or alkylene group has 1 to 24 carbon atoms. Inanother embodiment, an alkyl or alkylene group has 1 to 10 carbon atoms.A “lower alkyl” or “lower alkylene” group is a shorter chain alkyl oralkylene group, generally having one to six carbon atoms.

The term “carboxyl” or “carboxylate,” by itself or in combination withanother term contemplates a functional group containing carbon doublebonded to one oxygen molecule and single bonded to another oxygenmolecule. Common carboxyl or carboxylate groups have structures“—C(═O)O—” or OC(═O)— and “—OC(═O)O—” or —OC(═O)O—. Common carboxylatefunctional groups include but are not limited to carboxylic acids andesters.

The term “heteroalkyl,” by itself or in combination with another termcontemplates a stable straight or branched chain, or cyclic hydrocarbonradical, or combinations thereof, consisting of at least one carbon atomand at least one heteroatom selected from O, N, P, Si and S. As usedherein, the term “heteroatom” or “ring heteroatom” is meant to includeoxygen (O), nitrogen (N), sulfur (S), phosphorus (P), and silicon (Si).The N, P and S atoms may optionally be oxidized and the nitrogenheteroatom may optionally be quaternized. The heteroatom(s) O, N, P, Sand Si may be placed at any interior position of the heteroalkyl groupor at the position at which alkyl group is attached to the remainder ofthe molecule. Examples of heteroalkyl groups include, but are notlimited to, —CH₂CH₂OCH₃, —CH₂CH₂NHCH₃, —CH₂CH₂N(CH₃)CH₃, —CH₂SCH₂CH₃,—CH₂CH₂—, —S(O)CH₃, —CH₂CH₂S(O)₂CH₃, —CH═CHOCH₃,—Si(CH₃)₃, —CH₂CH═NOCH₃,—CH═CHN(CH₃)CH₃, —O—CH₃, —OCH₂CH₃, and —CN.Up to two or threeheteroatoms may be consecutive, such as, for example, —CH₂NHOCH₃ and—CH₂OSi(CH₃)₃.

The term “heteroalkylene” by itself or as part of another substituentcontemplates a divalent radical derived from heteroalkyl, asexemplified, but not limited by, —CH₂CH₂SCH₂CH₂— and —CH₂SCH₂CH₂NHCH₂—.For heteroalkylene groups, heteroatoms can also occupy either or both ofthe chain termini, e.g., alkyleneoxo, alkylenedioxo, alkyleneamino,alkylenediamino, and the like. Still further, for alkylene andheteroalkylene linking groups, no orientation of the linking group isimplied by the direction in which the formula of the linking group iswritten. For example, the formula —C(O)OR′— represents both —C(O)OR′—and —R′OC(O)—.

Heteroalkyl groups, as used herein, include those groups that areattached to the remainder of the molecule through a heteroatom, such as—C(O)R′, —C(O)NR′, —NR′R″, —OR′, —SR′, and/or —SO₂R′. Where“heteroalkyl” is recited, followed by recitations of specificheteroalkyl groups, such as —NR′R″ or the like, it will be understoodthat the terms heteroalkyl and —NR′R″ are not redundant or mutuallyexclusive. Rather, the specific heteroalkyl groups are recited to addclarity. Thus, the term “heteroalkyl” should not be interpreted hereinas excluding specific heteroalkyl groups, such as —NR′R″ or the like.

The terms “cycloalkyl” and “heterocycloalkyl”, by themselves or incombination with other terms, represent, unless otherwise stated, cyclicversions of “alkyl” and “heteroalkyl”, respectively. Additionally, forheterocycloalkyl, a heteroatom can occupy the position at which theheterocycle is attached to the remainder of the molecule. Examples ofcycloalkyl groups include, but are not limited to, cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclohexenyl, 3-cyclohexenyl,cycloheptyl, and the like. Examples of heterocycloalkyl groups include,but are not limited to, 1-(1,2,5,6-tetrahydropyridyl), 1-piperidinyl,2-piperidinyl, 3-piperidinyl, 4-morpholinyl, 3-morpholinyl,tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl,tetrahydrothien-3-yl, 1-piperazinyl, 2-piperazinyl, and the like. Theterms “cycloalkylene” and “heterocycloalkylene” refer to the divalentderivatives of cycloalkyl and heterocycloalkyl, respectively.

The terms “halo” or “halogen,” by themselves or as part of anothersubstituent, mean, unless otherwise stated, a fluorine, chlorine,bromine, or iodine atom. Additionally, terms such as “haloalkyl,” aremeant to include monohaloalkyl and polyhaloalkyl. For example, the term“halo(C₁-C₆)alkyl” is meant to include, but not be limited to,trifluoromethyl, 2,2,2-trifluoroethyl, 4-chlorobutyl, 3-bromopropyl, andthe like.

The term “aryl” means, unless otherwise stated, a polyunsaturated,aromatic, hydrocarbon substituent which can be a single ring or multiplerings (preferably from 1 to 3 rings) which are fused together or linkedcovalently. The term “heteroaryl” refers to aryl groups (or rings) thatcontain from one to four heteroatoms (in each separate ring in the caseof multiple rings) selected from N, O, and S, wherein the nitrogen andsulfur atoms are optionally oxidized, and the nitrogen atom(s) areoptionally quaternized. A heteroaryl group can be attached to theremainder of the molecule through a carbon or heteroatom. Non-limitingexamples of aryl and heteroaryl groups include phenyl, 1-naphthyl,2-naphthyl, 4-biphenyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl,2-imidazolyl, 4-imidazolyl, pyrazinyl, 2-oxazolyl, 4-oxazolyl,2-phenyl-4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl,5-isoxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-furyl, 3 -furyl,2-thienyl, 3-thienyl, 2-pyridyl, 3 -pyridyl, 4-pyridyl, 2-pyrimidyl,4-pyrimidyl, 5-benzothiazolyl, purinyl, 2-benzimidazolyl, 5-indolyl,1-isoquinolyl, 5-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl3-quinolyl,and 6-quinolyl. Substituents for each of above noted aryl and heteroarylring systems are selected from the group of acceptable substituentsdescribed below. The terms “arylene” and “heteroarylene” refer to thedivalent radicals of aryl and heteroaryl, respectively.

For brevity, the term “aryl” when used in combination with other terms,e.g., aryloxo, arylthioxo, arylalkyl, includes both aryl and heteroarylrings as defined above. Thus, the term “arylalkyl” is meant to includethose radicals in which an aryl group is attached to an alkyl group,e.g., benzyl, phenethyl, pyridylmethyl and the like, including thosealkyl groups in which a carbon atom, e.g., a methylene group, has beenreplaced by, for example, an oxygen atom, e.g., phenoxymethyl,2-pyridyloxymethyl, 3-(1-naphthyloxy)propyl, and the like.

Where a heteroalkyl, heterocycloalkyl, or heteroaryl includes a specificnumber of members, e.g. “3 to 7 membered,” the term “member” refers to acarbon or heteroatom.

The term “oxo” as used herein means an oxygen that is double bonded to acarbon atom.

Each of above terms, e.g., “alkyl,” “heteroalkyl,” “cycloalkyl, and“heterocycloalkyl,” “aryl,” “heteroaryl” as well as their divalentradical derivatives, are meant to include both substituted andunsubstituted forms of the indicated radical. Preferred substituents foreach type of radical are provided below.

Substituents for alkyl, heteroalkyl, cycloalkyl, heterocycloalkylmonovalent and divalent derivative radicals, including those groupsreferred to as alkylene, alkenyl, heteroalkylene, heteroalkenyl,alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, andheterocycloalkenyl, can be one or more of a variety of groups selectedfrom, but not limited to: —OR′, ═O, ═NR′, ═NOR′, —NR′R″, —SR′, -halogen,—SiR′R″R′″, —OC(O)R′, —C(O)R′, —CO₂R′, —C(O)NR′R″, —OC(O)NR′R″,—NR″C(O)R′, —NR′C(O)NR″R′″, —NR″C(O)OR′, —NRC(NR′R″)═NR′″, —S(O)R′,—S(O)₂R′, —S(O)₂NR′R″, —NRSO₂R′, —CN and —NO₂ in a number ranging fromzero to (2m′+1), where m′ is the total number of carbon atoms in suchradical. R′, R″, R′″ and R″″ each preferably independently refer tohydrogen, substituted or unsubstituted heteroalkyl, substituted orunsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl,substituted or unsubstituted aryl (e.g., aryl substituted with 1-3halogens), substituted or unsubstituted alkyl, alkoxy or thioalkoxygroups, or arylalkyl groups.

When a compound of the disclosure includes more than one R group, forexample, each of the R groups is independently selected as are each R′,R″, R′″ and R″″ groups when more than one of these groups is present.When R′ and R″ are attached to the same carbon or nitrogen atom, theycan be combined with the carbon or nitrogen atom to form a 4-, 5-, 6-,or 7-membered ring. For example, —NR′R″ is meant to include, but not belimited to, 1-pyrrolidinyl and 4-morpholinyl.

Similar to the substituents described for alkyl radicals above,exemplary substituents for aryl and heteroaryl groups as well as theirdivalent derivatives, are varied and are selected from, for example:halogen, —OR′, —NR′R″, —SR′, -halogen, —SiR′R″R′″, —OC(O)R′, —C(O)R′,—CO₂R′, —C(O)NR′R″, —OC(O)NR′R″, —NR″C(O)R′, —NR′C(O)NR″R′″,—NR″C(O)OR′, —NRC(NR′R″R′″)═NR″″, —NRC(NR′R″)═NR′″, —S(O)R′, —S(O)₂R′,—S(O)₂NR′R″, —NRSO₂R′, —CN, —NO₂, —N₃, —CH(Ph)₂, fluoro(C₁-C₆)alkoxo,and fluoro(C₁-C₆)alkyl, in a number ranging from zero to the totalnumber of open valences on aromatic ring system. In some embodiments,R′, R″, R′″ and R″″ are independently selected from hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl andsubstituted or unsubstituted heteroaryl.

The term “polymer” as used herein contemplates a molecule comprising ofone or more distinct types of structural repeat units. The term“polymer” as used herein is inclusive of “oligomer,” “copolymer,”“homopolymer” and like terms commonly known in the art. In someembodiments, the polymer is a cyclic polymer. In one embodiment, thecyclic polymer is cyclodextrin.

As used herein, the terms “repeat unit,” “structural unit,” and“structural repeat unit” are used interchangeably and will be understoodto mean the constitutional repeating unit (CRU), which is the smallestconstitutional unit the repetition of which constitutes a regularmacromolecule, a regular oligomer molecule, a regular block or a regularchain. As further used herein, the term “unit” will be understood tomean a structural unit which can be a repeating unit on its own, or cantogether with other units form a constitutional repeating unit.

The polymers and compounds disclosed herein may exist as salts. Examplesof applicable salt forms include hydrochlorides, hydrobromides,sulfates, methanesulfonates, nitrates, maleates, acetates, citrates,fumarates, tartrates (eg (+)-tartrates, (−)-tartrates or mixturesthereof including racemic mixtures), succinates, benzoates and saltswith amino acids such as glutamic acid. These salts may be prepared bymethods known to those skilled in art. Also included are base additionsalts such as sodium, potassium, calcium, ammonium, organic amino, ormagnesium salt, or a similar salt. When polymers of the presentdisclosure contain relatively basic functionalities, acid addition saltscan be obtained by contacting the neutral form of such compounds with asufficient amount of the desired acid, either neat or in a suitableinert solvent. Examples of acceptable acid addition salts include thosederived from inorganic acids like hydrochloric, hydrobromic, nitric,carbonic, monohydrogencarbonic, phosphoric, monohydrogenphosphoric,dihydrogenphosphoric, sulfuric, monohydrogensulfuric, hydriodic, orphosphorous acids and the like, as well as the salts derived organicacids like acetic, propionic, isobutyric, maleic, malonic, benzoic,succinic, suberic, fumaric, lactic, mandelic, phthalic, benzenesulfonic,p-tolylsulfonic, citric, tartaric, methanesulfonic, and the like. Alsoincluded are salts of amino acids such as arginate and the like, andsalts of organic acids like glucuronic or galactunoric acids and thelike.

The neutral forms of the polymer or compound may be regenerated bycontacting the salt with a base or acid and isolating the parentcompound in the conventional manner. The parent form of the polymerdiffers from the various salt forms in certain physical properties, suchas solubility in polar solvents.

The polymers and compounds disclosed herein can exist in unsolvatedforms as well as solvated forms, including hydrated forms. In general,the solvated forms are equivalent to unsolvated forms and areencompassed within the scope of the present disclosure. The polymersdisclosed herein may exist in multiple crystalline or amorphous forms.In general, all physical forms are equivalent for the uses contemplatedby the present disclosure and are intended to be within the scope of thepresent disclosure.

The polymers and compounds disclosed herein may possess asymmetriccarbon atoms (optical or chiral centers) or double bonds; theenantiomers, racemates, diastereomers, tautomers, geometric isomers,stereoisometric forms that may be defined, in terms of absolutestereochemistry, as (R)- or (S)- or, as (D)- or (L)- for amino acids,and individual isomers are encompassed within the scope of the presentdisclosure. The present disclosure includes compounds in racemic andoptically pure forms. Optically active (R)- and (S)-, or (D)- and(L)-isomers may be prepared using chiral synthons or chiral reagents, orresolved using conventional techniques. When the polymers disclosedherein contain olefinic bonds or other centers of geometric asymmetry,and unless specified otherwise, it is intended that the compoundsinclude both E and Z geometric isomers. The term “tautomer,” as usedherein, refers to one of two or more structural isomers which exist inequilibrium and which are readily converted from one isomeric form toanother. It will be apparent to one skilled in the art that certaincompounds described herein may exist in tautomeric forms, all suchtautomeric forms of the compounds being within the scope of theinvention.

Unless otherwise stated, structures depicted herein are also meant toinclude all stereo-chemical forms of the structure; i.e., the R and Sconfigurations for each asymmetric center. Therefore, singlestereochemical isomers as well as enantiomeric and diastereomericmixtures of the present compounds are within the scope of the invention.

The terms “a,” or “an,” when used in reference to a group ofsubstituents herein, mean at least one. For example, where a compound issubstituted with “an” alkyl or aryl, the compound is optionallysubstituted with at least one alkyl and/or at least one aryl. Moreover,where a moiety is substituted with an R substituent, the group may bereferred to as “R-substituted.” Where a moiety is R-substituted, themoiety is substituted with at least one R substituent and each Rsubstituent is optionally different.

As used herein, the term “about,” when referring to a value or to anamount of mass, weight, time, volume, concentration or percentage ismeant to encompass variations of ±20% or ±10%, more preferably ±5%, evenmore preferably ±1%, and still more preferably ±0.1% from the specifiedamount, as such variations are appropriate to perform the disclosedmethod.

The polymers of the present disclosure are within the principles ofchemical bonding known to those skilled in the art. Accordingly, where agroup may be substituted by one or more of a number of substituents,such substitutions are selected so as to comply with principles ofchemical bonding and to give compounds which are not inherently unstableand/or would be known to one of ordinary skill in the art as likely tobe unstable under ambient conditions, such as aqueous, neutral, andseveral known physiological conditions. For example, a heterocycloalkylor heteroaryl is attached to the remainder of the molecule via a ringheteroatom in compliance with principles of chemical bonding known tothose skilled in the art thereby avoiding inherently unstable compounds.

In one aspect, the present invention provides polymers capable ofdecomposing atmospheric ozone. The present invention also providescompositions comprising a solvent and an ozone decomposing polymer ofthe present invention, and methods of decomposing ozone by contactingozone with a polymer or composition of the present invention.

Ozone is a triatomic molecule composed of three oxygen atoms. It isformed from diatomic oxygen (O₂) by the action of sunlight, ultravioletlight or an electrical discharge. Scheme 1 illustrates the resonancestructures of triatomic ozone (O₃).

Ground level ozone pollution is created by the action of sunlight'sultraviolet rays on pollutants such as methane. An increase in groundlevel ozone levels can lead to respiratory problems (asthma andbronchitis and other lung diseases) and/or cause cardiopulmonaryproblems (heart attack). Long term exposure to ozone has been shown toincrease the risk of death. In addition, high levels of ozone in theatmosphere destroy the integrity of many elastomeric products found intires, such as natural rubber, polybutadiene, styrene-butadiene, andnitrile rubber, in a process known as “ozone-cracking.”

Nitrogen oxides (NO_(x)) in the atmosphere also react with volatileorganic compounds in the air to form ozone in sunlight. The generatedozone can react with other things, such as plants or rubber to producemore volatile organic compounds. These volatile compounds are releasedinto the air and ultimately produce more ozone. The polymers describedhere are designed to decompose ozone, and stop this process.

In a second aspect, the present invention provides ozone decomposingcompounds of Formula I, Formula II, or Formula III:

and salts and solvates thereof, wherein:

n is an integer from 1-10, and

each R¹ and R² is independently hydrogen, substituted or unsubstitutedalkyl, substituted or unsubstituted perfluoroalkyl, substituted orunsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl,substituted or unsubstituted aryl, substituted or unsubstitutedheteroaryl, substituted or unsubstituted arylalkyl, substituted orunsubstituted heteroarylalkyl, substituted or unsubstituted—(CH₂)_(j)CN, substituted or unsubstituted —(CH₂)_(j)OR³, substituted orunsubstituted —(CH₂)_(j)C(O)R³, substituted or unsubstituted—(CH₂)_(j)OC(O)R⁴, substituted or unsubstituted —(CH₂)_(j)C(O)OR³,substituted or unsubstituted —(CH₂)_(j)OC(O)OR³, substituted orunsubstituted —(CH₂)_(j)NR⁵R⁶, substituted or unsubstituted—(CH₂)_(j)C(O)NR⁵R⁶, substituted or unsubstituted —(CH₂)_(j)OC(O)NR⁵R⁶,substituted or unsubstituted —(CH₂)_(j)NR⁵C(O)R⁴, substituted orunsubstituted —(CH₂)_(j)NR⁵C(O)OR³, substituted or unsubstituted—(CH₂)_(j)NR⁵C(O)NR⁵R⁶, substituted or unsubstituted—(CH₂)_(j)S(O)_(m)R⁷, substituted or unsubstituted—(CH₂)_(j)NR⁴S(O)_(m)R⁷, or substituted or unsubstituted—(CH₂)_(j)S(O)_(m)NR⁵R⁶,

wherein each j is independently an integer from 0 to 6; each m isindependently an integer from 0 to 2; each n is independently an integerfrom 0 to 4; or

each R¹ is as described above, and each R² is independently an acrylicmonomer or polymer, an alkyd monomer or polymer, an epoxy monomer orpolymer, a vinyl monomer or polymer or a cellulose monomer or polymer;

R³ is independently hydrogen, or substituted or unsubstituted alkyl;

R⁴ and R⁷ are each independently hydrogen, or substituted orunsubstituted alkyl;

R⁵ and R⁶ are each independently hydrogen, substituted or unsubstitutedalkyl, or R⁵ and R⁶, together with the N atom to which they areattached, form a 5- or 6-membered heterocyclic ring or a 5-memberedheteroaryl ring; and

wherein each R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ group is optionallyindependently substituted with 1-3 substituents, each independentlyselected from alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl,perfluoroalkyl, amide, amino, alkylamino, carboxylate, cyano,dialkylamino, halogen, hydroxyl, imino, nitro, oxo, sulfide, and thiol.

In one embodiment the present invention provides an ozone decomposingcompound of Formula VII, Formula VIII, or Formula IX:

wherein each R₁ and n is as defined above.

In another aspect, the present invention provides an ozone decomposingcomposition comprising a solvent and a polymer comprising a structuralrepeat unit of Formula X, Formula XI, or Formula XII, wherein thepolymer decomposes ozone:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides an ozone decomposingcompound of Formula XIII, Formula XIV, or Formula XV:

wherein n is an integer from 1-10; and

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl.

In another aspect, the present invention provides ozone decomposingcompositions comprising a solvent and a polymer comprising a structuralrepeat unit of Formula XVI, Formula XVII, or Formula XVIII:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides ozone decomposingcompositions comprising a solvent and a polymer comprising a structuralrepeat unit of Formula XIX, Formula XX, or Formula XXI:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides ozone decomposingcompositions comprising a solvent and a polymer comprising a structuralrepeat unit of Formula XXII, Formula XXIII, or Formula XXIV:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides ozone decomposingcompositions comprising a solvent and a polymer comprising a structuralrepeat unit of Formula XXV, Formula XXVI, or Formula XXVII:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides ozone decomposingcompositions comprising a solvent and a polymer comprising a structuralrepeat unit of Formula XXVIII, Formula XXIX, or Formula XXX:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides ozone decomposingcompositions comprising a solvent and a polymer comprising a structuralrepeat unit of Formula XXXI, Formula XXXII, or Formula XXXIII:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides ozone decomposingcompositions comprising a solvent and a polymer comprising a structuralrepeat unit of Formula XXXIV, Formula XXXV, or Formula XXXVI:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides compounds of FormulaIV, Formula V, or Formula VI:

and salts and solvates thereof, wherein:

n is an integer from 1-10, and

each R¹ and R² is independently hydrogen, substituted or unsubstitutedalkyl, substituted or unsubstituted perfluoroalkyl, substituted orunsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl,substituted or unsubstituted aryl, substituted or unsubstitutedheteroaryl, substituted or unsubstituted arylalkyl, substituted orunsubstituted heteroarylalkyl, substituted or unsubstituted—(CH₂)_(j)CN, substituted or unsubstituted —(CH₂)_(j)OR³, substituted orunsubstituted —(CH₂)_(j)C(O)R³, substituted or unsubstituted—(CH₂)_(j)OC(O)R⁴, substituted or unsubstituted —(CH₂)_(j)C(O)OR³,substituted or unsubstituted —(CH₂)_(j)OC(O)OR³, substituted orunsubstituted —(CH₂)_(j)NR⁵R⁶, substituted or unsubstituted—(CH₂)_(j)C(O)NR⁵R⁶, substituted or unsubstituted —(CH₂)_(j)OC(O)NR⁵R⁶,substituted or unsubstituted —(CH₂)_(j)NR⁵C(O)R⁴, substituted orunsubstituted —(CH₂)_(j)NR⁵C(O)OR³, substituted or unsubstituted—(CH₂)_(j)NR⁵C(O)NR⁵R⁶, substituted or unsubstituted—(CH₂)_(j)S(O)_(m)R⁷, substituted or unsubstituted—(CH₂)_(j)NR⁴S(O)_(m)R⁷, or substituted or unsubstituted—(CH₂)_(j)S(O)_(m)NR⁵R⁶,

wherein each j is independently an integer from 0 to 6; each m isindependently an integer from 0 to 2; each n is independently an integerfrom 0 to 4; or

each R¹ is as described above, and each R² is independently an acrylicmonomer or polymer, an alkyd monomer or polymer, an epoxy monomer orpolymer, a vinyl monomer or polymer or a cellulose monomer or polymer;

R³ is independently hydrogen, or substituted or unsubstituted alkyl;

R⁴ and R⁷ are each independently hydrogen, or substituted orunsubstituted alkyl;

R⁵ and R⁶ are each independently hydrogen, substituted or unsubstitutedalkyl, or R⁵ and R⁶, together with the N atom to which they areattached, form a 5- or 6-membered heterocyclic ring or a 5-memberedheteroaryl ring; and

wherein each R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ group is optionallyindependently substituted with 1-3 substituents, each independentlyselected from alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl,perfluoroalkyl, amide, amino, alkylamino, carboxylate, cyano,dialkylamino, halogen, hydroxyl, imino, nitro, oxo, sulfide, and thiol.

In another aspect, the present invention provides methods fordecomposing ozone by contacting ozone with an ozone decomposing compoundof Formula I, Formula II, or Formula III:

or a salt or solvate thereof, wherein:

n is an integer from 1-10; and

R¹ and R² are each independently hydrogen, substituted or unsubstitutedalkyl, substituted or unsubstituted perfluoroalkyl, substituted orunsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl,substituted or unsubstituted aryl, substituted or unsubstitutedheteroaryl, substituted or unsubstituted arylalkyl, substituted orunsubstituted heteroarylalkyl, substituted or unsubstituted—(CH₂)_(j)CN, substituted or unsubstituted —(CH₂)_(j)OR³, substituted orunsubstituted —(CH₂)_(j)C(O)R³, substituted or unsubstituted—(CH₂)_(j)OC(O)R⁴, substituted or unsubstituted —(CH₂)_(j)C(O)OR³,substituted or unsubstituted —(CH₂)_(j)OC(O)OR³, substituted orunsubstituted —(CH₂)_(j)NR⁵R⁶, substituted or unsubstituted—(CH₂)_(j)C(O)NR⁵R⁶, substituted or unsubstituted —(CH₂)_(j)OC(O)NR⁵R⁶,substituted or unsubstituted —(CH₂)_(j)NR⁵C(O)R⁴, substituted orunsubstituted —(CH₂)_(j)NR⁵C(O)OR³, substituted or unsubstituted—(CH₂)_(j)NR⁵C(O)NR⁵R⁶, substituted or unsubstituted—(CH₂)_(j)S(O)_(m)R⁷, substituted or unsubstituted—(CH₂)_(j)NR⁴S(O)_(m)R⁷, or substituted or unsubstituted—(CH₂)_(j)S(O)_(m)NR⁵R⁶,

wherein each j is independently an integer from 0 to 6; each m isindependently an integer from 0 to 2; each n is independently an integerfrom 0 to 4; or

each R¹ is as described above, and each R² is independently an acrylicmonomer or polymer, an alkyd monomer or polymer, an epoxy monomer orpolymer, a vinyl monomer or polymer or a cellulose monomer or polymer;

R³ is independently hydrogen, or substituted or unsubstituted alkyl;

R⁴ and R⁷ are each independently hydrogen, or substituted orunsubstituted alkyl;

R⁵ and R⁶ are each independently hydrogen, substituted or unsubstitutedalkyl, or R⁵ and R⁶, together with the N atom to which they areattached, form a 5- or 6-membered heterocyclic ring or a 5-memberedheteroaryl ring; and

wherein each R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ group is optionallyindependently substituted with 1-3 substituents, each independentlyselected from alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl,perfluoroalkyl, amide, amino, alkylamino, carboxylate, cyano,dialkylamino, halogen, hydroxyl, imino, nitro, oxo, sulfide, and thiol.

In one embodiment of this aspect, the present invention provides methodsfor decomposing ozone by contacting ozone with an ozone decomposingcompound of Formula VII, Formula VIII, or Formula IX:

wherein each R₁ and n is as defined above.

In another aspect, the present invention provides methods fordecomposing ozone comprising contacting ozone with an ozone decomposingcomposition, wherein said composition comprises a solvent and a polymercomprising a structural repeat unit of Formula X, Formula XI, or FormulaXII:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another embodiment, the present invention provides methods fordecomposing ozone by contacting ozone with an ozone decomposingcompound, wherein the compound has Formula XIII, Formula XIV, or FormulaXV:

wherein n is an integer from 1-10; and each R₁ is independently selectedfrom the group consisting of hydrogen, substituted or unsubstitutedalkyl, substituted or unsubstituted heteroalkyl, substituted orunsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl,substituted or unsubstituted aryl, substituted or unsubstitutedheteroaryl, substituted or unsubstituted arylalkyl, and substituted orunsubstituted heteroarylalkyl.

In another aspect, the present invention provides methods fordecomposing ozone comprising contacting ozone with an ozone decomposingcomposition, wherein said decomposing composition comprises a solventand a polymer comprising a structural repeat unit of Formula XVI,Formula XVII, or Formula XVIII:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides methods fordecomposing ozone comprising contacting ozone with an ozone decomposingcomposition, wherein said composition comprises a solvent and a polymercomprising a structural repeat unit of Formula XIX, Formula XX, orFormula XXI:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another embodiment, the present invention provides methods fordecomposing ozone comprising contacting ozone with an ozone decomposingcomposition, wherein said composition comprises a solvent and a polymercomprising a structural repeat unit of Formula XXII, Formula XXIII, orFormula XXIV:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides methods fordecomposing ozone comprising contacting ozone with an ozone decomposingcomposition, wherein said composition comprises a solvent and a polymercomprising a structural repeat unit of Formula XXV, Formula XXVI, orFormula XXVII:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another embodiment, the present invention provides methods fordecomposing ozone comprising contacting ozone with an ozone decomposingcomposition, wherein said composition comprises a solvent and a polymercomprising a structural repeat unit of Formula XXVIII, Formula XXIX, orFormula XXX:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides methods fordecomposing ozone comprising contacting ozone with an ozone decomposingcomposition, wherein said composition comprises a solvent and a polymercomprising a structural repeat unit of Formula XXXI, Formula XXXII, orFormula XXXIII:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In another aspect, the present invention provides methods fordecomposing ozone comprising contacting ozone with an ozone decomposingcomposition, wherein said composition comprises a solvent and a polymercomprising a structural repeat unit of Formula XXXIV, Formula XXXV, orFormula XXXVI:

wherein m is an integer from 100 to 100,000;

n is an integer from 1-10;

each R₁ is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl, substituted or unsubstitutedheteroalkyl, substituted or unsubstituted cycloalkyl, substituted orunsubstituted heterocycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted heteroaryl, substituted or unsubstitutedarylalkyl, and substituted or unsubstituted heteroarylalkyl; and

wherein the structural repeat unit comprises at least 50% by weight ofthe polymer.

In one aspect the present invention provides an ozone reactive polymercomprising a structural repeat unit represented by the following formulaXLI:

wherein

A is absent or a linking group selected from the group consisting ofsubstituted or unsubstituted alkylene, substituted or unsubstitutedheteroalkylene, substituted or unsubstituted cycloalkylene, substitutedor unsubstituted heterocycloalkylene, substituted or unsubstitutedarylene, substituted or unsubstituted heteroarylene, substituted orunsubstituted arylalkylene, and substituted or unsubstitutedheteroarylalkylene;

each of R₁, R₂ and R₃ is, independently, selected from the groupconsisting of hydrogen, substituted or unsubstituted alkyl, substitutedor unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl,substituted or unsubstituted heterocycloalkyl, substituted orunsubstituted aryl, substituted or unsubstituted heteroaryl, substitutedor unsubstituted arylalkyl, and substituted or unsubstitutedheteroarylalkyl; and

wherein said structural repeat unit comprises at least 10% by weight ofsaid polymer.

With respect to each of the polymers of the present invention, in someembodiments, the repeat unit comprises at least 10% by weight of thepolymer. In other embodiments the structural repeat unit comprises atleast 20% by weight of the polymer, while in other embodiments thestructural repeat unit comprises at least 30% by weight of the polymer,and in still other embodiments the structural repeat unit comprises atleast 40% by weight of the polymer. In certain embodiments thestructural repeat unit comprises at least 50% by weight of the polymer,and in certain other the structural repeat unit comprises at least 60%by weight of the polymer. In yet other embodiments the structural repeatunit comprises at least 70% by weight of the polymer. In still otherembodiments the structural repeat unit comprises at least 80% by weightof the polymer, and in still other embodiments the structural repeatunit comprises at least 90% by weight of the polymer.

Ozone reacts with alkenes and alkynes to form organic compounds in aprocess known as ozonolysis. The multiple bonds in these compounds areoxidized by the action of ozone to provide compounds in which the doublebonds have been replaced with oxygen. The outcome of the reactiondepends on the type of multiple bonds being oxidized. For example,alkenes can be oxidized by ozone to form alcohols, aldehydes, ketones,or carboxylic acids. Typically, two aldehydes and/or ketones areproduced when the olefinic compound is appropriately substituted. Scheme2 illustrates an ozonolysis reaction between a carbon-carbon double bondand ozone. The reaction provides two aldehydes and/or ketones dependingupon the R₃-R₆ substituents.

The term “aldehyde,” as used herein, is given its well-known meaning inthe field of organic chemistry, comprising the substituent —CH═O.Similarly, the term “ketone,” as used herein, refers to a chemicalcompound comprising the substituent —C(═O)—.

The combustion of fossil fuels produces a group of pollutants, such asmethane and other hydrocarbons, which are known to be ozone precursors.Ground level ozone pollution is created by the action of sunlight'sultraviolet rays on these precursors. An increase in ground level ozonelevels can lead to respiratory problems (asthma and bronchitis and otherlung diseases); and cause cardiopulmonary problems (heart attack). Longterm exposure to ozone has been shown to increase the risk of death. Inaddition, high levels of ozone in the atmosphere destroy the integrityof many elastomeric products found in tires, such as natural rubber,polybutadiene, styrene-butadiene, and nitrile rubber, in a process knownas “ozone-cracking.”

Nitrogen oxides (NO_(x)) in the atmosphere also react with volatileorganic compounds in the air to form ozone in sunlight. The generatedozone can react with other things, such as plants or rubber to producemore volatile organic compounds. These volatile compounds are releasedinto the air and ultimately produce more ozone. The compounds describedherein stops this process.

Thus, the polymers described herein, such as those comprising astructural unit represented by the general formula XLI, reacts withozone at the site of the double bond to provide two aldehydes or twoketones or one aldehyde and one ketone. The nature of the aldehydes andketones formed by the reaction depends on the side chains R₁ and R₂ incompounds of formula XLI. Thus, the by-products produced upon reactionwith atmospheric ozone is controlled based on the side chains R₁ and R₂.In one embodiment, one of the aldehydes or ketones is attached to thepolyol or sugar derivative, and the other aldehyde or ketone is attachedto a monomer or polymer. As used herein, the term “sugar” refers todigestible mono- and disaccharides. Non-limiting examples are glucose,dextrose, sucrose, lactose, maltose and fructose.

Neither of the resulting compounds volatize into the air and therefore,the inhalation of both ozone and dangerous aldehydes such asformaldehyde, is reduced or eliminated. The aldehyde or ketone polyol orsugar derivatives produced does not cause a negative environmentalimpact. Moreover, surfaces coated with the compounds described hereinare saturated with the presence of double bonds, which are present ingreater concentration than other paints or clothing. This greaterconcentration increases the reaction with ozone, and helps reduce ozonelevels both indoors and outdoors.

In one embodiment, the structural repeat unit is represented by theformula XLII

In another embodiment, the structural repeat unit is represented by theformula XLIII

In some embodiments, the structural repeat unit of formula XLI comprisesat least 10% by weight of the polymer. In some embodiments, thestructural unit of formula XLI comprises at least 20%, at least 30%, atleast 40%, at least 50%, at least 60%, at least 70%, at least 80%, atleast 90%, or at least 99% by weight of the polymer. In a preferredembodiment, the structural unit of formula XLI comprise between 60% and90% by weight of the polymer.

In some embodiments, the polymer decomposes ozone at a rate at least twotimes faster than in the absence of the polymer. In some embodiments,the polymer has a weight average molecular weight ranging from 9,000 to30,000 Daltons.

In some embodiments, the primary by-product formed upon reaction of thepolymer disclosed herein with ozone is a non-volatile compound. In someof these embodiments, the non-volatile compound is sugar. In otherembodiments, the non-volatile compound is vanillin. In some embodiments,the primary by-product is a compound that emits a scent.

In some embodiments, the primary by-products formed upon reaction of thepolymer disclosed herein with ozone is a volatile compound. In some ofthese embodiments, the volatile by-products are safe and non-toxic tohumans. Non-limiting examples of such volatile by-products arebenzaldehyde, citral, vanillin, raspberry ketone and camphor.

In some embodiments, described herein is a coating comprising the ozonereactive polymer. In some of these embodiments, the said coating is aspray coating.

In some embodiments, the polymers disclosed herein are incorporated ontoclothing, fabrics, carpets, paints, sealants, finishes, air-filters,face-masks, cosmetics, creams, lotions, and coatings. In someembodiments, such incorporation results in the clothing, fabric, carpet,paints, sealants, finishes, and coatings having the ability to decomposeozone. Polymers make up the majority of the composition of the paintexposed to the atmosphere, so the reactions with the ozone are muchfaster the more they are exposed to the atmosphere.

The compounds described throughout this disclosure can be used inseveral forms. In some embodiments, the polymers described herein arepresent in a spray or aerosol. When the presence of ozone is known orsuspected, the spray can be sprayed in that area. In other embodiments,the polymers described in this disclosure may be used as a coating onsurfaces. In this case, when ozone comes in contact with the surface,the double bonded side chain in the polymer reacts with the ozone andreduces the level of ozone. The polymer coating described herein may bevisible, invisible, may have texture, or may not have texture. In someembodiments, the polymers of this disclosure are present in a paint.

In one aspect the present invention provides a method for decomposingozone comprising contacting ozone with an ozone decomposing composition,wherein said composition comprises a solvent and a polymer comprising astructural repeat unit represented by the following formula XLI:

wherein

A is absent or a linking group selected from the group consisting ofsubstituted or unsubstituted alkylene, substituted or unsubstitutedheteroalkylene, substituted or unsubstituted cycloalkylene, substitutedor unsubstituted heterocycloalkylene, substituted or unsubstitutedarylene, substituted or unsubstituted heteroarylene, substituted orunsubstituted arylalkylene, and substituted or unsubstitutedheteroarylalkylene;

each of R₁, R₂ and R₃ is, independently, selected from the groupconsisting of hydrogen, substituted or unsubstituted alkyl, substitutedor unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl,substituted or unsubstituted heterocycloalkyl, substituted orunsubstituted aryl, substituted or unsubstituted heteroaryl, substitutedor unsubstituted arylalkyl, and substituted or unsubstitutedheteroarylalkyl; and

and wherein said structural repeat unit comprises at least 10% by weightof said polymer.

In one embodiment of this aspect, the structural repeat unit isrepresented by the formula XLII:

In another embodiment of this aspect, the structural repeat unit isrepresented by the formula XLIII:

In some embodiments, the structural repeat unit of formula XLI compriseat least 10% by weight of the polymer. In some embodiments, thestructural repeat unit of formula XLI comprise at least 20%, at least30%, at least 40%, at least 50%, at least 60%, at least 70%, at least80%, at least 90%, or at least 99% by weight of the polymer. In oneembodiment, the structural repeat unit of formula XLI comprise between60% and 90% by weight of the polymer.

In some embodiments, the polymer decomposes ozone at a rate faster thanin the absence of the polymer. In some of these embodiments, the polymerdecomposes ozone at a rate at least two times faster than in the absenceof the polymer. In some embodiments, the polymer has a weight averagemolecular weight ranging from 9,000 to 30,000 Daltons. In someembodiments, the primary by-product upon reaction of the polymer withozone is a non-volatile compound. In some of these embodiments, thenon-volatile compound is sugar. In some of these embodiments, thenon-volatile compound is vanillin. In some embodiments, the primaryby-product upon reaction with ozone is a compound that emits a scent.

Paint is used to decorate, protect and prolong the life of natural andsynthetic materials, and acts as a barrier against environmentalconditions. Paints contain pigments to impart color and opacity; binders(resin) or polymers that form a matrix to hold the pigment in place;extenders or larger pigment particles added to improve adhesion andstrength; solvents (thinners) such as an organic solvent or water toreduce the viscosity of the paint for better application; and additivesto modify the properties of the liquid paint or dry film. Most paintscontain polymers that act as binders for pigments which give paintstheir characteristic color. These polymers, however, are relativelyunreactive towards ozone. By contrast, the compounds of the presentdisclosure react with ozone in the atmosphere, which thereby reducesozone levels. In addition, the ozonolysis reaction produces safe byproducts, e.g. aldehydes and ketones.

The most important binders (resins) or polymers used in modern paintsare: acrylic polymers; alkyd polymers; and epoxy polymers.

Acrylic polymers are used in many emulsion paints. These polymers arebased on co-polymerization of vinyl acetate with a propenoate ester. Asshown in Scheme 3, vinyl acetate (1) can react withmethyl-2-methyl-propenoate (2) to form a random array of linear chainedacrylic polymers (3) and (4).

In the above polymerization reaction, the value of m can be controlledto give a range of resins varying from viscous liquids to solids withhigh melting points. Other acrylic esters commonly used as co-monomerswith vinyl acetate include, but are not limited to, methyl propenoate,ethyl propenoate, propyl propenoate, butyl propenoate and stereoisomersthereof.

The compounds of Formula I, II, or III can be incorporated into aderivatized vinyl monomer and undergo similar polymerization reactions.As described above, the double bonds in these polymers can be oxidizedby the action of ozone, to provide various aldehyde and/or ketoneproducts.

The derivatized vinyl monomers can be prepared as shown in Scheme 4.Ethyl acetate (5) can react with a compound of Formula IV, V or VI inthe presence of base, followed by acidification, to provide theunsaturated ester (6) through an Aldol condensation reaction. Reductionof the unsaturated ester (6) with LiAlH₄ provides the correspondingallyl alcohol, which upon treatment with [Ir(cod)Cl]₂/Na₂CO₃ in thepresence of vinyl acetate [Organic Syntheses, Vol. 82, p. 55 (2005)],provides the derivatized vinyl monomer (7).

As shown below, the derivatized vinyl monomers produced by the reactionsequence outlined in Scheme 4, include the compounds of Formula VII,Formula VIII, and Formula IX.

As shown in Scheme 5, the derivatized vinyl monomer compound (7) canpolymerize to form a random array of linear chain polymers (8).

As shown below, the polymers produced by the polymerization reactionoutlined in Scheme 5, include the compounds of Formula X, Formula XI,and Formula XII.

As shown in Scheme 6, a typical alkyd polymer resin used in gloss paintscan be produced by reacting benzene-1,2-dicarboxylic (phthalic)anhydride (9) with a suitably substituted monoglyceride (10) and adrying oil (linseed or soybean oil). When heated together, esterlinkages are formed to provide the alkyd polymer (11):

In the above polymerization reaction, the value of m can be controlledto give a range of resins varying from viscous liquids to solids withhigh melting points.

The compounds of Formula I, II, or III can be incorporated into amonoglyceride monomer and undergo similar polymerization reactions withphthalic anhydride. As described above, the double bonds in thesepolymers can be oxidized by the action of ozone, to provide variousaldehyde and/or ketone products.

As shown in Scheme 7, the derivatized monoglyceride monomers can beprepared through an Aldol condensation reaction. The hydroxyl groups onmonoglyceride-2-acetate (10) can be diprotected usingtert-butyldimethylsilyl chloride (TBSCl) in the presence of base(N,N-diisopropylethylamine) to generate the corresponding TBS ethers.Reaction of the diprotected compound with a compound of Formula IV, V orVI in the presence of base, followed by acidification provides theunsaturated ester (12) through an Aldol condensation reaction. Reductionof the unsaturated ester (12) with a catalytic amount of InBr₃ andexcess Et₃SiH [J. Org. Chem., 2007, 5920-5922], and deprotection of theTBS protecting groups with tetra-n-buylammonium fluoride (TBAF) providesthe derivatized monoglyceride monomer (13).

As shown below, the derivatized monoglyceride monomers produced by thereaction sequence outlined in Scheme 7, includes the compounds ofFormula XIII, Formula XIV, and Formula XV.

As shown in Scheme 8, benzene-1,2-dicarboxylic (phthalic) anhydride (9)can react with the modified monoglyceride monomers (13) to provide thealkyd polymer (14).

As shown below, the derivatized vinyl ether monomers produced by thepolymerization reaction outlined in Scheme 8, includes the compound ofFormula XVI, Formula XVII, and Formula XVIII.

Epoxy resins are often used as the binder in industrial coatings orprimers. They give paint excellent adhesion properties together withhigh resistance to chemicals (corrosion). As shown in Scheme 9,substituted phenols such as bisphenol A (15) and1-chloro-2,3-epoxypropane (16) can be used to prepare the epoxy resin(17).

In the above polymerization reaction, the value of m can be controlledto give a range of resins varying from viscous liquids to solids withhigh melting points. Epoxy resin formulations can be carried in solventssuch as aromatic hydrocarbons, alcohols, ketones and esters or asdispersions in water as true emulsions. They are not normally used intopcoats for outdoors because they are susceptible to UV degradation,but they make excellent interior coatings and exterior primers.

The compounds of Formula I, II, or III can be incorporated into an epoxyresin through the free hydroxyl groups present on these polymers. Asdescribed above, the double bonds in these polymers can be oxidized bythe action of ozone, to provide various aldehyde and/or ketone products.

As shown below in Scheme 10, the epoxy resin (17) can be modified byacylation of the hydroxyl group with acetic anhydride and base, followedby Aldol condensation with a compound of Formula IV, V or VI in thepresence of base, followed by acidification, and reduction of theunsaturated ester with a catalytic amount of InBr₃ and excess Et₃SiH toprovide the derivatized epoxy resin (18).

In the above polymerization reaction, the value of m can be controlledto give a range of resins varying from viscous liquids to solids withhigh melting points. As shown below, the derivatized epoxy resinproduced by the polymerization reaction outlined in Scheme 10, includethe compounds of Formula XIX, Formula XX, and Formula XXI.

Vinyl polymers are a group of polymers derived from vinyl monomers andare the most commonly used type of plastics. As shown below in Scheme11, vinyl polymers can be prepared from their corresponding monomers,and include but are not limited to polymers such as polyethylene,polypropylene, polybutadiene, polystyrene, polyvinyl acetate, polyvinylalcohol, and polyvinyl chloride

In the above polymerization reaction, the value of n can be controlledto give a range of resins varying from viscous liquids to solids withhigh melting points. The compounds of Formula I, II, or III can beincorporated into these types of vinyl polymers by similar proceduresknown to those of skill in the art. As described above, the double bondsin these polymers can be oxidized by the action of ozone, to providevarious aldehyde and/or ketone products.

For example, the compounds of Formula I, II, or III can be incorporatedinto a polyalkyl halide. As shown below in Scheme 12, reaction of apolyalkyl halide (19) with Ph₃P forms an ylide, which reacts with acompound of Formula IV, V or VI through a Wittig coupling procedure toprovide the olefinic polymer (20).

In the above polymerization reaction, the value of m can be controlledto give a range of resins varying from viscous liquids to solids withhigh melting points. As shown below, the olefinic polymer produced bythe polymerization reaction outlined in Scheme 12, include the compoundsof Formula XXII, Formula XXIII, and Formula XXIV.

Cellulose is a polysaccharide consisting of a linear chain of severalhundred to over ten thousand β(1-4) linked D-glucose units. Cellulose isthe most abundant organic polymer and is found as a structural componentin many plants. It also found in many fabrics, for example, thecellulose content of cotton fiber is about 90%.

As shown below in Scheme 13, cellulose may be modified to incorporatethe compounds of Formula I, II, or III through a Witting reactionsequence. For example, reaction of cellulose (21) in the presence ofdilute acid (HCl) and Ph₃P forms an ylide, which reacts with a compoundof Formula IV, V or VI through a Wittig coupling procedure to providethe olefinic polymer (22).

In the above polymerization reaction, the value of m can be controlledto give a range of resins varying from viscous liquids to solids withhigh melting points. As shown below, the olefinic polymer produced bythe polymerization reaction outlined in Scheme 13, include the polymerscomprising a structural repeat unit of Formula XXV, Formula XXVI,Formula XXVII, Formula XXVIII, Formula XXIX, or Formula XXX.

Alternatively, the compounds of Formula I, II, or III can beincorporated into cellulose (21) through the sequence shown in Scheme14. Acylation of the primary alcohols in cellulose (21), followed byAldol condensation of the corresponding acetates with a compound ofFormula IV, V or VI, and reduction of the carbonyl group as previouslydescribed, provides the derivatized cellulose polymer (23).

In the above polymerization reaction, the value of m can be controlledto give a range of resins varying from viscous liquids to solids withhigh melting points. As shown below, the derivatized cellulose polymerproduced by the polymerization reaction outlined in Scheme 14, includespolymers comprising a structural repeat unit of Formula XXXI, FormulaXXXII, Formula XXXIII, Formula XXXIV, Formula XXXV, or Formula XXXVII,where each R₁, m and n is as defined above.

In some embodiments, the polymers and compounds described herein areused in conjunction with other means to remove ozone and/or other typesof pollution. These means include, but are not limited to, metals thatbind to carbon monoxide, metal nanoparticles or traces of metal forfurther oxidation or reduction of sulfur oxides and nitrogen oxides inthe presence of sunlight, hydroxides that react with sulfur oxides,nitrogen oxides, ammonia, carbon dioxide, hydrogen sulfide, and otherair pollutants, and other highly reactive functional groups.

In some embodiments, the side chains of the polymers and compoundsdescribed herein are altered in order to adjust its polarity.Alterations include, but is not limited to, addition or deletion of ahydrocarbon group, phenyl groups, alcohols, carboxylic acids, or anyother functional group or side chain group. Different polarities havedifferent advantages. For example, one polarity may allow for bettermixing, while another polarity may allow rain to be less or moreabsorbed.

In some embodiments, the polymers described herein undergo color changesupon reaction with ozone. In other embodiments, upon reaction withozone, fragrant compounds, such as cinnamaldehyde or vanillin areproduced. This fragrance indicate that the reaction is working. In someembodiments, the polymers described herein has a varying degree ofsmoothness or texture. In some embodiments, the side chains in thepolymers are altered such that it reacts with water or other solvents toa varying degree.

In some embodiment, the polymers and compounds described herein areadded to a paint. In these embodiments, the paint helps minimizeenvironmental effects caused by ozone. In some of these embodiments, thepolymers and additives also increase the paint strength and adhesion.

The compounds described herein can also be attached to any of thefollowing including but not limited to: pigments, additives,cross-linker or polymer resin group, co-vehicles, solvent, and any othercategory added to paints, adhesives, or coating agents.

The presence of double bonds in the polymers and compounds describedherein allow for reaction with ozone in the atmosphere to form aldehydesor ketones compounds. This reaction is shown in Scheme 15. The additionof double bonds or incorporation of double bonds, or use of doublebonded polymers, cross-linkers, co-vehicles, additives, pigments, orother groups added to the paint that might associate with thecross-linkers or polymers, will be exposed to the atmosphere. Thesegroups may be hydrophobic or hydrophilic, or both. In addition, the useof double bonded molecules that might act as one, two, or severaldifferent categories, and might chemically bind additives, pigments,polymer resins, co-vehicles, solvents, and other categories added topaint.

In the polymers and compounds described herein, the addition of a doublebonded or unsaturated molecule may be comprised in or attached tocross-linkers, polymers, co-vehicles, solvents, additives, and pigments,and incorporated into paint, such that upon reaction with ozone, it doesnot produce harmful volatile organic compounds. This may also includeunsaturated vitamins, flavonoids, carotenoids, and other naturalunsaturated molecules found in the environment and plants that willreact with ozone to produce non-volatile organic compounds. An exampleof this is Vitamin C which reacts with ozone to produce dehydroascorbicacid. Other products that can be performed maybe salts, a molecule witha high boiling point or melting point, contain charges that keep it fromvolatilizing, be safe or non-harmful to human health, may form a gassuch as nitrogen gas or other gases, produce no or less negativeenvironmental impacts upon washing away due to rain, maybe beneficial tothe environment such as helping the soil or organisms in the soil, maycreate molecules that be used as anti-fouling agents, creates moleculesthat do not produce volatile organic compounds that will eventuallyproduce more ozone, creates volatile organic compounds upon reactionwith ozone that are non-toxic, are used for fragrant smells such asaromatic compounds, beneficial or neutral to the environment, allows thepaint to breathe whether expand or contract that maybe beneficial to thepaint coating, or forms a secondary reactive agent such as hydroxylradicals that may react with other air pollutants.

The polymers and compounds described herein can be attached to orcomprised in the cross-linkers or polymeric resin of a paint. Becausethe cross-linkers or polymers are what holds up the paint to the walland are the molecules exposed to the atmosphere, this is the group thatwill react with the ozone. The use of double bonded polymers that do notrelease any by-products upon reaction with ozone, such as when thedouble bond is attached on both sides to a polymer or some othermolecules that upon reaction with ozone will form ketones and aldehydesthat will stay attached and be incorporated into the paint, and thepaint or bonding agent does not degrade over time.

In some embodiments, the polymers described herein are incorporated intospheres or other structures that might provide a higher surface areasuch as fullerenes, or other compounds. A further example is if eachside chain contains multiple unsaturated bonds that allows for evengreater reactivity towards ozone.

In the compounds and polymers described herein, the use of double bondedmolecules attached to polymers, cross-linkers, emulsifiers, additives,pigments, and any other group added to paint that upon reaction withozone does not destroy the molecule itself, but only a side chain. Forexample, if oleic acid is used in the paint as the polymer, but ozonereacts with it, it will be turned into two by-products. If a saturatedpolymer is used but double bonded molecules are added to the polymer,then upon reaction with ozone, side chains will fall off, but thepolymer chain will still function properly and not affect the paint oradhesive bonding agent.

In the compounds disclosed herein, the incorporation of differentmixtures of polymers or cross-linkers that constitute differentpercentages based on the different qualities of the paint that want tobe produced. For example, the cross-linker or polymeric resin canconstitute that has ozone reducing compounds attached may constitute1-100 percent composition, while other polymeric cross-linkers maybeadded to change its polarity, allow it to breathe better, change itsstructure, allow it to dissolve or be incorporated into paint mixturesbetter, or other reasons not specified.

In some embodiments, the compounds and polymers described herein arepresent in paint. In these embodiments, the amount of polymer orcrosslinker in the paint can vary from 0% to 99%. Other ingredientspresent in paint are emulsifier (0% to 99%), solvent (0% to 99%),additives (0% to 99%), and pigments (0% to 99%).

In some embodiments, the compounds, polymers, and methods described canbe incorporated into clothing, glues, and adhesives, or incorporated asa coating on carpets, fabrics, wallpaper, and paint.

The following examples are provided to further illustrate theembodiments of the present disclosure, but are not intended to limit thescope of the disclosure. While they are typical of those that might beused, other procedures, methodologies or techniques known to thoseskilled in the art may alternatively be used.

EXAMPLE 1 Synthesis of Glucose Derivative and Vanillin Derivative ofPoly (Vinyl Alcohol) (PVOH)

Glucose derivative and vanillin derivative of polymer vinyl alcohol weresynthesized according to the following 2-step reaction as shown inScheme 16.

Step 1. Synthesis of Polymer A via Esterification of PVOH withBromoacetyl Bromide. PVOH (5.2418 g, 80 mmol OH groups) was dissolved inDMAc/5 wt % LiCl solvent system (150 mL) at 80° C. The solution wascooled down to room temperature and charged into a three-necked flaskequipped with a nitrogen inlet and outlet, dropping funnel, magneticstirrer and thermometer. Pyridine (9.71 mL, 120 mmol) was added to theflask as an acid acceptor. DMAc solution (80 mL) containing bromoacetylbromide (10.45 mL, 120 mmol) was then added dropwise at about 0° C. withstirring. The reaction mixture was then reacted at room temperature for18 h. After reaction, the solution was poured into large amount of 2MHCl (1.2 L) to precipitate the product. The precipitated product wasfiltered and washed three times with cold distilled water, and driedunder vacuum oven at 50° C. to constant weight. In this example shown inscheme 16, the number of “y” structural units in the polymer is aboutfour times the number of “x” structural units.

Step 2 for Synthesis of Polymer B via Wittig Reaction of BromoacetylatedPVOH (Polymer A) with Glucose. Polymer A (3 g, 16.09 mmol Br groups) andTPP (5.06 g, 19.29 mmol) was dissolved in THF (120 g), then water (60 g)was added into above solution. The solution was kept at 60° C. for 1hour. TEA (2.4 g, 23.71 mmol) and glucose (5.4 g, 29.97 mmol) werecharged. The reaction mixture was then reacted at 60° C. for 87 hours.The bottom layer was collected, washed with heptane, THF, isopropanol,dichloromethane, and vacuum dried at 50° C. to constant weight.

Step 2 for Synthesis of Polymer C via Wittig Reaction of BromoacetylatedPVOH (Polymer A) with Vanillin. Polymer A (100 mg, 0.536 mmol Brgroups), TPP (253.21 mg, 0.965 mmol), and vanillin (122 mg, 0.804 mmol)were charged into saturated sodium bicarbonate solution (10 mL). Thesolution was kept at 25 oC for 65 hours. The color of the reactionmixture changed after the reaction. A solid powder was obtained afterdrying

Scheme 16: Synthesis of Polymer A (bromoacetylated PVOH), Polymer B(glucose derivative of poly vinyl alcohol), and Polymer C (vanillinderivative of PVOH) from polyvinyl alcohol.

EXAMPLE 2 Characterization of Glucose Derivative of Poly(Vinyl Alcohol)

FTIR and NMR characterization of bromoacetylated PVOH (polymer A) showedthat all the hydroxyl group of the polyvinyl alcohol disappeared afteresterification by bromoacetyl bromide. New resonance peak at around 5.05ppm in NMR indicated the success of the esterification of polyvinylalcohol with bromoacetyl bromide.

FTIR and NMR characterization of glucose derivative of polyvinyl alcohol(polymer B) showed the hydroxyl group formation, which comes fromglucose, and also the double bond formation which comes from the Wittigreaction. NMR resonance peaks at around 6.2 ppm and 6.6 ppm alsoindicated double bond formation and the success of the Wittig reactionof glucose with bromoacetylated PVOH.

EXAMPLE 3 Ozonolysis of Polymer B (Glucose Derivative of PVOH)

An ozone generator, ozone meter, and fan were put inside a 20 literstorage container (polyvinylethylene and polyvinyl propylene). Anycracks or openings in the container were sealed off with tape. For theblank run, the fan was turned on and the ozone level was measured withthe ozone meter every 30 seconds. For the negative control, the ozonegenerator was turned on until ozone level reached 10 ppm, and thenunplugged it. The degradation of ozone due to random reactions (such asrubber extension cords in the box) was monitored.

For the positive controls, polymer B was dispersed in water and appliedon the surfaces of the inside of the container. While it took about 1minute to reach 10 ppm ozone concentration in the negativeconcentration, in the presence of polymer B it took 4 minutes to reacharound 4.5 ppm ozone concentration. This indicated that the generatedozone reacted with the polymer during the charging, which caused thelonger time to reach certain level of ozone. The decay of ozoneconcentration was monitored and recorded every 30 seconds. Ozonolysisresults showed that in the presence of polymer B, it took about 4minutes to decrease the ozone concentration to zero, whereas it tookabout 10 minutes to decrease the ozone concentration to zero in theabsence of polymer B.

EXAMPLE 4 Ozonolysis of Polymer B (Glucose Derivative of PVOH) GeneratesAldehydes or Ketones

0.1 g of the polymer B was mixed in 40 mL of water, stirring vigorously.An ozone generator was used to pump ozone into the beaker for 30minutes. This resembled atmospheric conditions where atmospheric water,double bonds and ozone react together to form aldehydes and/or ketones.NMR spectra showed that as the reaction was progressing a peak formed˜10 ppm, indicating that an aldehyde formed upon reaction of the polymerwith ozone. At the same time, the NMR peak at 6-7 ppm, which is from thedouble bonds present in the polymer, disappeared slowly. Once thereaction completed, the aldehyde peaks disappeared indicating thatglucose has been produced.

EXAMPLE 5 A Spray Comprising Polymer B

5 g of polymer B, 32 ounces of water and a few drops ofdetergent/emulsifier were mixed together to form a solution. Thissolution was put in a spray bottle. This spray is useful for decomposingand removing ozone.

EXAMPLE 6 By-Products of the Reaction of Polymer and Ozone Acts as anAir Scrubber

When the double bond of the polymer described herein reacts with ozone,it forms an ozonide. This ozonide decomposes instantaneously as a resultof atmospheric water vapor to form aldehydes and/or ketones, dependingon the structure of the molecule. The other byproducts formed arehydroxyl radicals. These hydroxyl radicals are only present for a splitsecond because they are so reactive and react with virtually anything.For this reason hydroxyl radicals are known as an air scrubber, whichremoves air pollution from the air. For example, it reacts with methane,formaldehyde, and carbon monoxide to form carbon dioxide. It also reactsand oxidizes halogenated chemicals that can hurt the ozone layer, andinitiate the removal of these relatively non-reactive chemicals from theair. Other reactions may include further oxidizing nitrogen oxides,volatile organic compounds, and sulfur oxides. For these reasons, theyare an important part of Earth's atmospheric chemistry. In this way, thepolymers described herein may be used to remove atmospheric contaminantsbesides ozone.

While the present disclosure has been described and illustrated herein,it is intended that the specification and examples be considered asexemplary only, with the true scope and spirit of the invention beingindicated by the following claims.

What is claimed is:
 1. An ozone decomposing composition comprising asolvent and a polymer, wherein the polymer comprises a structural repeatunit selected from the group consisting of Formula X, Formula XI,Formula XII, Formula XVI, Formula XVII, Formula XVIII, Formula XIX,Formula XX, Formula XXI, Formula XXII, Formula XXIII, Formula XXIV,Formula XXV, Formula XXVI, Formula XXVII, XXVIII, Formula XXIX, FormulaXXX, Formula XXXI, Formula XXXII, or Formula XXXIII, Formula XXXIV,Formula XXXV, and Formula XXXVI:

wherein: m is an integer from 100 to 100,000; n is an integer from 1-10;and each R₁ is independently selected from the group consisting ofhydrogen, substituted or unsubstituted alkyl, substituted orunsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl,substituted or unsubstituted heterocycloalkyl, substituted orunsubstituted aryl, substituted or unsubstituted heteroaryl, substitutedor unsubstituted arylalkyl, and substituted or unsubstitutedheteroarylalkyl.
 2. The polymer of claim 1, wherein said structuralrepeat unit comprises at least 50% by weight of said polymer.
 3. Thepolymer of claim 1, wherein said structural repeat unit comprises atleast 80% by weight of said polymer.
 4. The polymer of claim 1, wherein,upon reaction with ozone, a non-volatile compound is produced.
 5. Thepolymer of claim 4, wherein the non-volatile compound is a sugar.
 6. Thepolymer of claim 1, wherein, upon reaction with ozone, a compound thatemits a scent is produced.
 7. The polymer of claim 6, wherein thecompound that emits a scent is vanillin.
 8. A method of decomposingozone comprising contacting ozone with the ozone decomposing compositionof claim
 1. 9. The method of claim 8, wherein said polymer has a weightaverage molecular weight of 9,000 to 30,000 Daltons.
 10. The method ofclaim 8, wherein, upon reaction with ozone, a non-volatile compound isproduced.
 11. The method of claim 10, wherein said non-volatile compoundis a sugar.
 12. The method of claim 8, wherein, upon reaction withozone, a compound that emits a scent is produced.
 13. The method ofclaim 12, wherein the compound that emits a scent is vanillin.
 14. Acoating comprising a solvent and the ozone decomposing polymer ofclaim
 1. 15. The coating of claim 14, wherein said coating is a spraycoating.
 16. A composition selected from the group consisting of an itemof clothing, a fabric, a carpet, a paint, a sealant, a finish, anair-filter, a face-mask, a cosmetic, a cream, a lotion, and a coating,wherein the composition incorporates the ozone decomposing polymer ofclaim
 1. 17. The composition of claim 16, which is an air-filter. 18.The composition of claim 16, selected from the group consisting of acosmetic, a cream, and a lotion.